I'd investigate trying to use both hands; I know it feels really odd at first but if you persevere it can pay dividends. You can practice the hold and angles using a butter knife. Take it easy around the chin and concentrate on the angle; don't let the razor go too steep; and use very light very short strokes.

In regards to frequency, there's probably little benefit to shaving more often than one needs to, other than the pure entertainment :-)

In regards to the fine, soft hairs, I have a light beard growth (I could never grow a full beard) and have some light, soft hairs around the lips; and I'm 52 not a college student like you. I sometimes tackle these with a DE (I use a DE maybe once or twice a week) but, as has been mentioned, if your razor is truly sharp it should cut them.

Carl